


Preview - Welcome to Underground City

by Khurious



Category: Undertale (Video Game)
Genre: 1920's, Blowjobs, Cigar Use, Drug Addiction, Drug Use, F/M, Female Reader, Gangsters, Multi, NSFW, Skeletons In Suits, alternative universe, mafia, not safe for work
Language: English
Status: Completed
Published: 2016-01-06
Updated: 2016-01-18
Packaged: 2018-05-12 03:27:25
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,199
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5650861
Author URL: https://archiveofourown.org/users/Khurious/pseuds/Khurious
Summary: <blockquote class="userstuff">
              <p>This is a preview for a long term fanfiction I am writing featuring the Undertale cast in a 1920's like world. Monsters were never banished under Mt. Ebott, instead monsters and humans live together, but no one ever said it was easy. This features your "interaction" with the main cast. ;)</p><p>You are the main character!<br/>Let me know what you think!</p><p>(**NSFW**)</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This sample which takes place midway through the main story, sorry if things don't make too much sense! It will in the grand scheme of things!

Shuffling through papers, W.D. Gaster let out a deep groan, a rumbling through his skeletal chest. Numbers were not adding up, orders were not getting to their needed locations. Muffet had mailed him two letters now, many of her customers had yet to receive their monthly quota. He pushed forward at his desk, the chair wheels squeaking in protest as they were prevented from move in any further under the desk. Resting his elbows on the stained wood, he held his head in his hands. He pulled down his hat; a dark black fedora laced with a white ribbon. A gift from Catty and Bratty down at their boutique, a gift for helping prevent further damage to their store front. Those humans wouldn’t be returning anytime soon. He pulled out a black silken handkerchief; embossed with a large G, a gift from you, and dabbed around the collar of his turtleneck. You certainly weren’t making this any easier for him.

A knock echoed in the darkened room, only lit by a small lamp at the corner of his desk. He prefered his office to be dark at the moment, he even drew the blinds. He glanced over at his watch, ah yes, Papyrus and Sans should be here. He huffed, then took in a deep breath… exhaling slowly, hoping to calm himself. Lifting up the papers at his desk, his breath hitched, his grip tightening on the papers a bit more than he meant to. A slight wrinkle formed under his grip. He looked down at himself, his turtleneck was still slightly tucked into dark dress pants, but overall he looked professional. He had an organization to run after all, just because you were in the picture didn’t mean he could slack up on his appearance.

He hesitated for a moment, not glancing up. Stay calm, he repeated to himself, stay calm. “Come **_in_ ** …” He bit down on his teeth causing quite an audible click, swallowing a groan. He glared down at his desk before him, huffing out one final time as the door opened. He didn’t glance up, keeping his stare down towards the paper. “Glad to see you two here on time. Thank you for keeping the two of you on a tighter schedule, Papyrus.” Their shoes came into view under the brim of his hat, but he did not meet their gazes. He did not see it, but he knew, Papyrus saluted happily before him, the satin suspenders straining at the position. “No problem sir! I also made sure Frisk got to his room safe and sound!” Placing the papers down and lacing his bony fingers, he rested his head forward. “Execellent. Any news you two would like to share?”

The two before him went quiet, only the smoke of Sans’s cigar filled the air. The smell of the smoke always reminded you of toasted marshmallows. Papyrus rocked on his feet, his black and red wingtipped shoes creaking back and forth as he swayed. The white and blue wingtipped shoes kicked at the ground a bit, before coming up to lean against the desk. “well, boss…” Sans started repeating information Gaster already knew, just confirming his suspicions. Still no word on the missing orders, supplies were running out at each selling locations, and Alphys has yet to reply to any contact attempt. He had a bad feeling, but perhaps it was time for a personal visit to the scientist. He had about a month left of supplies, then he would run dry.

He held up his right hand, a motion to be silent. Sans grin faltered, he was just a second away from a pun, somehow Gaster always seemed to know when they were coming. Gaster’s dark magic flared, both eyes flashing a bit too bright for liking and he was quick to summon phantom hands to gather papers throughout the cabinets behind him. His two subordinates standing before him glanced towards each other, boss was acting pretty odd. Usually he’s quite meticulous about the filing, preferring to do it all on his own. “Um, Boss, are you feeling well?” Papyrus asked in a softer more inside voice, not wanting to make Gaster mad if he was feeling unwell. Gaster took a deep breath, exhaling slowly once more, “ **_Ah_ ** ,” he let slip a pant a bit louder than he wanted, “ _Yes,”_ he hissed out, “Just in need of a bit de-stressing. Here.” Two ghostly hand holding papers hovered in front of the skeleton brothers, Papyrus grabbed both sets when Sans didn’t move to grab his. “Read these and report back to me in an hour, bring Frisk.” He instructed as a phantom hand to open the door behind them.

Shrugging to each other, Papyrus and Sans turned heel and left, only Sans hesitating at the door for a moment. A quiet sound of jingling caught a certain skeleton’s attention, and he huffed out smoke to hinder his laughter; it was a sound he come to know quite well. Before closing it, Sans turned back to the boss with a questionable look, only for it to twist into a smirk. The boss was shifting about in his chair, eyes knitted shut with his mouth slightly apart. He was panting, gripping the desk. “ **_Nghhh_ ** …” Well, at least the boss wasn’t gonna be _bonely_ for the hour. Sans closed the door with a chuckle, following after Papyrus down the hall. “Come on lazy bones! We can’t have the boss mad again for boondoggling!” As much as Papyrus tries to use an indoor voice, it never really lasts long. Gaster frowned as he panted, a much needed moan finally escaping his lips once the two left. This was your fault, distracting him from his work.

“ **_Ahk_ **!” He gasped out quite loudly, thrusting his hips forward, groaning your name under his breath. A heated dark blush dancing across his white skull face, a tongue threatening to loll out. A coughing and whimper came out from under the desk and he slowly rolled his chair back. A skeletal grin creeped across his face as he pulled out his handkerchief to dab his face. “Well, my pet…” He panted out and whipped his mouth, catching any drool which may have escaped. His chest rumbled at the sight of your chesire grin which shined out from under the desk’s darkness. You crawled out from underneath, your collar’s silver bell singing your arrival. You were dressed only in a white dress shirt with pressed cuffs and collar around the neck, black panties to hide your lower secrets. You always dressed nice for Mister Gaster. The blackened aura cum dripped down your chin as you held most of it in your mouth. It had no taste, but had body, like melted ice cream. “I believe this time you deserve a reward.” He smiled to himself, you were always quite the de-stresser for him when he felt anxious. You helped him clear his mind. He pulled open a drawer to the left side of your head as you sat patiently, sweat dripping down your forehead. Your vision had a slight haze to it, unable to focus.

In between his two fingers he held a small red round candy, a “candy” stamped with a large letter D. You slid your tongue out, the spectral ooze dripping down your shirt; unable to stain it in its incorporeal form. Gaster chuckled, lifting the opposite hand to hold up back your hair which threatened to fall forward. He loved to watch you, loved watching your eyes. He held his fingers down to your face and you gladly took the treat into your mouth, as well as the two fingers holding it. He shivered as you began to weave in between the bone phalanges, whimpering quietly as you did so. Your body was feeling terribly hot, the area between your legs throbbing with need. The candy jumped between his fingers, rolling around on your tongue. The candy did not melt, but clicking against your teeth started to chip away its outer shell. He pulled his fingers back, a trail of saliva and cum creating a bridge between you and the finger tips. “Go ahead, swallow it.” You always waited for permission.

You gulped it all down, the candy piece and cum, feeling both dissipate once it slid down your throat. You tremble, a shiver biting down your spine. The heat started in your belly, blossoming outwards to your toes, to your fingers, and to your head. Your eyes became sharp, the haze fading away instantly. Your cheeks formed a light crimson coloring as you leaned back against the inside of the desk. Spasms and waves filled you, causing a bit of delirium as your body ingested the feeling. Your panting was quite loud in the silent room, pupils dilating and focusing, repeating the process as you tried to regain your senses properly. You felt confident, you felt powerful, you felt awake, and you felt alive. You were filled with… _determination_.

Gaster’s ghostly hands, ones that you once feared, started caressing your body. A moan escaped your lips as you felt them poke and prod against your skin. Each touch left your skin feeling tingly and yet numb, like static. You spread your legs out of sheer habit, the fingers of one hand pushing against your panties. Gaster’s eyes watched over you, enjoying the display. “My dear, I am afraid we do not have time for more fun.” You cried out; a mix of despair and from the pressure of the fingers against your entrance. Boss was always such a tease to you. Gazing up at him, you pouted and groaned as your own hands made their way towards your crotch. If he wasn’t going to help your need, then you might as well.

However you must be forgetting, he is the boss after all. As your fingers inched towards your entrance, you found them suddenly pinned to the sides of the desk with a rather loud thump. Looking up at Gaster you whimper, tears dancing in your vision. “M-Master… please. You know what the candy does to me…” The candy, your own personal nickname for it, was not a sweet treat to enjoy. It was determination in pill form, something Gaster’s organization had been working on for years. His scientist, Alphys, and Gaster himself created them out of pure scientific research. Funny how it became one of the cities most sought after addiction. The feelings it brought in you were indescribable. Too bad to the general public it was unavailable, unless they found other means of the source… a source Gaster was happily to supply. The illegal drug trade of determination was a rather wealthy one if you played your cards right.   

 He chuckles, and you nearly scream as he presses the heel of his shoe against your weeping entrance, pressing the panties roughly against you. The force isn’t too rough, but the pressure combined with your burning need caused you to thrust your hips upwards, your pulsating clit grinding against it. His cracked skull smiled as he forced his heel down harder. “G-Gaster!” You cried out, struggling against his magical bindings. “This is for teasing me in front of the boys my dear. Quite rude of you.” He chided you as he rubbed his shoe up and down, then slowly in circles. You were getting close, the determination only heightening your closing in orgasm. Closer; the burning between your hips nearly reaching its peak. _Closer_ ; you cry out, arching your back, you were nearly there. **Closer** ; your lower abdomen contracting and tightening like a coil. **_Closer_ ** …

Gaster pulled back his shoe and crossed his legs, the slightly damp shoe dangling now a few feet above your body. You panted, whining, thrusting your hips up towards him. Except there was no more pleasure, nothing to snuff the craving and put out the fire. He called out your name and you looked up to him, meeting his burning purple eyes. His magic scared you before, but now, you craved what his magic could do to you. His magic, Sans’s, even Papyrus’s, each of their own magics knew exactly what to do to you to drive you crazy. “ **_G_ ** \- **_Gaster_ ** ...   **_please_ ** …” You cried out to him, and his bindings on your wrist disappeared.

He had a weakness for you. He sat back, patting his lap and you crawled up to him. Straddling his legs, the front of the panties pressing against his opened fly. His erection rubbed against you, pressing into the clit once more. He held you down on his lap as your legs threatened to bounce you, the need for friction great. Softly he stroked under your chin, jingling the bell on your collar. Property of W.D. Gaster read the tag on the underside, a rather comically drawn skull facing the front. It faced forward for all to see, for all to be warned of just who you were and who you belonged to. Being the beloved pet of the most wanted mafia syndicate in Underground City had its perks after all.


	2. The Adventure Begins... Over There!

**Care to see where this story, your story, begins?**

**Follow the link below!**

**<http://archiveofourown.org/works/5760310> **

**Author's Note:**

> I love the idea of the Undertale cast in a mafia like setting!  
> Sorry this was so short, it was just a sample! More in the future!
> 
> Here's some images that really inspired me:  
> http://40.media.tumblr.com/1bf24b98ce8f632c9bc7271c99ebe0a1/tumblr_nygjygSDPV1tyciswo1_1280.jpg  
> http://i.imgur.com/dLjgwdh.jpg  
> http://40.media.tumblr.com/46a53d456374e249d78c373546b1eec7/tumblr_nwkai1sUKA1se3952o2_1280.png  
> Let me know what you think, and don't forget to check out my current long running Undertale story; A Change In Heart, I'll be working on both at the same time :)


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